Single step synthesis of strigolactone analogues from cyclic keto enols, germination stimulants for seeds of parasitic weeds

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 16, 2011, Pages 5006-5011

  Mwakaboko, Alinanuswe S ^a   Zwanenburg, Binne ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

Bioassay; Germination; Orobanche; Parasitic weeds; Striga; Strigolactone

Indexed keywords

2 (HYDROXYMETHYL) 5 [(4 METHYL 5 OXO 2,5 DIHYDRO 2 FURANYL)OXY] 4H PYRAN 4 ONE; 2 METHYL 3 [(4 METHYL 5 OXO 2,5 DIHYDRO 2 FURANYL)OXY] 4H PYRAN 4 ONE; 3 METHYL 5 [(3 OXOX 1 CYCLOHEXENYL)OXY] 2(5H) FURANONE; 4 [(4 METHYL 5 OXO 2,5 DIHYDRO 2 FURANYL)OXY] 2H CHROMEN 2 ONE; 5 [(5,5 DIMETHYL 3 OXO 1 CYCLOHEXENYL)OXY] 3 METHYL 2(5H) FURANONE; 6 METHYL 4 [(4 METHYL 5 OXO 2,5 DIHYDRO 2 FURANYL)OXY] 2H PYRAN 2 ONE; LACTONE DERIVATIVE; STRIGOLACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOASSAY; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; GAS CHROMATOGRAPHY; GERMINATION; MASS SPECTROMETRY; MOLECULAR DYNAMICS; NONHUMAN; OROBANCHE; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; STRUCTURE ACTIVITY RELATION; SYNTHESIS; WEED; WITCHWEED;

GERMINATION; LACTONES; OROBANCHE; PLANT PREPARATIONS; PLANT WEEDS; SEEDS; STRIGA;

OROBANCHE; OROBANCHE CERNUA; STRIGA; STRIGA HERMONTHICA;

EID: 79961172369     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.06.057     Document Type: Article

References (49)

1. C. Parker Pest Manag. Sci. 65 2009 453 and refs cited therein
2. S.J. Hearne Pest Manag. Sci. 65 2009 603 and refs cited therein
3. C.E. Cook, L.P. Whichard, B. Turner, M.E. Wall, and G.H. Egley Science 154 1966 1189
4. C.E. Cook, L.P. Whichard, M.E. Wall, G.H. Egley, P. Coggon, P.A. Luhan, and A.T. Mcphail J. Am. Chem. Soc. 94 1972 6189
5. C. Hauck, S. Müller, and H. Schildknecht J. Plant physiol. 139 1992 474
6. B.K. Siame, K. Wood, G. Ejeta, Y. Weerasuriya, and L.G. Butler J. Agric. Food Chem. 41 1993 1486
7. T. Yokota, H. Sakai, K. Okuno, K. Yoneyama, and Y. Takeuchi Phytochemistry 49 1998 1967
8. Y. Koichi, X. Xie, K. Yoneyama, and Y. Takeuchi Pest Manag. Sci. 65 2009 467
9. X. Xie, K. Yoneyama, and K. Yoneyama Annu. Rev. Phytopathol. 48 2010 93
10. K. Yoneyama, A.A. Awad, X. Xie, K. Yoneyama, and Y. Takeuchi Plant Cell Physiol. 51 2010 1095
11. A.W. Johnson, G. Gowda, A. Hassanali, J. Knox, S. Monaco, Z. Razavi, and G. Roseberry J. Chem. Soc., Perkin Trans. I 1981 1734
12. A. Hassanali Strigol Analogues: Synthetic Achievements and Prospects E.S. Ayensu, H. Doggett, K.D. Keynes, J. Marton-Lefevre, L.J. Musselman, C. Parker, A. Peckering, Striga, Biology and Control 1984 ICSU Press Paris 125 132
13. E.M. Mangnus, and B. Zwanenburg J. Agric. Food Chem. 40 1992 1066
14. B. Zwanenburg, E.M. Mangnus, J.W.J.F. Thuring, Strigol Analogues: Design Synthesis and Biological Activity, in: A.H. Pieterse, J.A.C. Verkley, S.J. Terborg (Eds.), Proceedings of the Third International Workshop on Orobanche and Related Striga Research, Royal Tropical Institute, Amsterdam, (1994) 187-197.
15. A. Kranz, E. Samson-Schulz, L. Hennig, P. Welzel, D. Muller, H. Mayer-Figge, and W.S. Sheldrick Tetrahedron 52 1996 14827
16. E.M. Mangnus, and B. Zwanenburg Recl. Trav. Chim. Pays-Bas 111 1992 155
17. E.M. Mangnus, L.A. Van Vliet, D.A.L. Vandenput, and B. Zwanenburg J. Agric. Food Chem. 40 1992 1222
18. J.W.J.F. Thuring, G.H.L. Nefkens, and B. Zwanenburg J. Agric. Food Chem 45 1997 1409
19. B. Zwanenburg, A.S. Mwakaboko, A. Reizelman, G. Anilkumar, and D. Sethumadhavan Pest Manag. Sci 65 2009 478
20. For some total syntheses of natural SLs, see: G.A. MacAlpine, R.A. Raphael, A. Shaw, A. Taylor, and H.J. Wild J. Chem. Soc., Chem. Perkin Trans 1976 410
21. Y. Sugimoto, S.C.M. Wigchert, J.W.J.F. Thuring, and B. Zwanenburg J. Org. Chem 63 1998 1259
22. J. Matsui, T. Yokota, M. Bando, Y. Takeuchi, and K. Mori Eur. J. Org. Chem. 1999 2201
23. A. Reizelman, M. Scheren, G.H.L. Nefkens, and B. Zwanenburg Synthesis 2000 1944
24. Y. Kondo, E. Tadokoro, M. Matsuura, K. Iwasaki, Y. Sugimoto, H. Miyake, H. Takikawa, and M. Sasaki Biosci., Biotechnol., Biochem. 71 2007 2781
25. C. Bhattacharya, P. Bonfante, A. Deagostino, Y. Kapulnik, P. Larini, E.G. Occhiato, C. Prandi, and P. Venturello Org. Biomol. Chem. 7 2009 3413
26. G.H.L. Nefkens, J.W.J.F. Thuring, M.F.M. Beenakkers, and B. Zwanenburg J. Agric. Food Chem. 45 1997 2273
27. A.S. Mwakaboko, and B. Zwanenburg Plant Cell Physiol 52 2011 699
28. For improved syntheses GR 24, see: E.M. Mangnus, F.J. Dommerholt, R.L.P. de Jong, and B. Zwanenburg J. Agric. Food Chem. 40 1992 1230
29. H. Malik, F.P.J.T. Rutjes, and B. Zwanenburg Tetrahedron 66 2010 7198
30. A.W. Johnson, G. Roseberry, and C. Parker Weed Res. 16 1976 223
31. R.E. Eplee, and R.S. Norris Chemical Control of Striga L.J. Musselman, Parasitic Weeds in Agriculture Vol 1 Striga 1987 CRC Press Baca Raton, FL, USA 173 182
32. C. Parker, and C.R. Riches Parasitic Weeds of the World, Biology and Control 1993 CAB International Wallingford, Oxon, UK
33. E.M. Mangnus, P.L.A. Stommen, and B. Zwanenburg J. Plant Growth Regul 11 1992 91
34. D. Rubiales, M. Fernández-Aparicio, K. Wegmann, and D.M. Joel Weed Res. 49 2009 23
35. S.C.M. Wigchert, E. Kuiper, G.J. Boelhouwer, G.H.L. Nefkens, J.A.C. Verkleij, and B. Zwanenburg J. Agric. Food Chem. 47 1999 1705
36. A.G.T. Babiker, A.M. Hamdoun, A. Rudwan, N.G. Mansi, and H.H. Faki Weed Res. 27 1987 173
37. A.G.T. Babiker, N.E. Ibrahim, and W.G. Edwards Weed Res. 28 1988 1
38. A.R. Saghir, Dormancy and germination of Orobanche seeds in relation to control methods, in: S.J. Terborg, (Ed.), Biology and Control of Orobanche Proceedings of a workshop in Wageningen, 1986, sage, Thenetherlands, pp. 25-34.
39. K. Akiyama, K.-I. Matsuzaki, and H. Hayashi Nature 435 2005 824
40. K. Akiyama, S. Ogasawara, S. Ito, and H. Hayashi Plant Cell Physiol. 51 2010 1104
41. H.J. Bouwmeester, C. Roux, J.A. Lopez-Raez, and G. Bécard Trends Plant Sci. 12 2007 224
42. V. Gomez-Roldan, S. Fermas, P.B. Brewer, V. Puech-Pages, E.A. Dun, J.-P. Pillot, F. Letisse, R. Matusova, S. Danoun, J.-C. Portais, H. Bouwmeester, G. Becard, C.A. Beveridge, C. Rameau, and S.F. Rochange Nature 455 2008 189
43. M. Umehara, A. Hanada, S. Yoshida, K. Akiyama, T. Arite, N. Takeda-Kamiya, H. Magome, Y. Kamiya, K. Shirasu, K. Yoneyama, J. Kyozuka, and S. Yamaguchi Nature 455 2008 195
44. Y. Tsuchiya, and P. McCourt Curr. Opin. Plant Biol. 12 2009 556
45. C.Y. Chen, J.H. Zou, S.Y. Zhang, D. Zaitlin, and L.H. Zhu Sci. China Ser C-Life Sci. 52 2009 693
46. D.M. Burness Org. Synth. 4 1963 628
47. D.M. Burness Org. Synth. 4 1963 649
48. G.H.L. Nefkens, J.W.J.F. Thuring, and B. Zwanenburg Synthesis 1997 290
49. H. Malik, F.P.J.T. Rutjes, and B. Zwanenburg Synthesis 2010 3271